My First Time

by 30YearOldVirgin

What’s your gender? Woman
How old are you? 30
What’s your race/ethnicity? East Asian
What continent do you live on? Europe
What country and/or city do you live in? United Kingdom
Highest education received: Post-graduate degree (currently pursuing)
What’s your occupation? Student
What’s your current relationship status? Single
Religious affiliation:
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 1
How many hookup stories have you here posted before? 0

My First Time

How long ago did this hookup happen? A few weeks ago

What was your relationship status at the time? Dating casually

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? For less than a week

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? I was in a club for a birthday party and we spotted each other. I thought he was hot. He “came to my rescue” when I couldn’t get the bartenders’ attention and later helped me carry drinks to my table.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We chatted after he helped me with my drinks. As the night went on, my friends started to give us some space and we were talking at a corner. He gave me a kiss and he was grabbing me all over. Even though I wanted him then, I was hesistant as I was still a virgin, so I gave him my number and went home without him.

We texted for a few days. Each night, I’d masturbate because our texts were getting wild. He expressed that he really wanted to fuck me, so I told him to come by.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? He came over my house and I commented about how it has been cold. He grabbed my hands and started to blow hot air on it to warm it up. We didn’t even manage to exchange many words before he started to kiss me, saying that this will warm me up. Afraid that my housemates would see me making out at the front door, I took him to my room and he started to peel off his coat while I kept my singlet and shorts on. He pushed me onto my bed and his hands were immediately exploring my body. His hands were strong, big and rough. He pushed down my singlet and bra to expose my breasts and hungrily suck at them.

The scruffy stubbles he had on his face scratched me while his tongue gave me gentle licks, it was an intense feeling. To give better access, I took my top and bra off, sat on him and lowered my breasts to his face. He happily pinched and sucked my nipples while I rubbed my crotch against his. The friction caused by his pants and my shorts was enough to get him hard very quickly. As I was enjoying all the love my breasts was getting, he asked if I want to be fingered and I guided his hands down my pants. I opened my shorts and showed off the lace panties I had on for him and I could tell he loved it. While he kept his mouth latched on to my breast, he peeled off my panties and started to touch my vagina. To be honest, this was my first time getting fingered by someone else, and the sensation of heat and his rough fingers were unexpected. I closed my eyes to try and make sense of what I was feeling while I got fingered. We didn’t say anything during this time, all I could hear was our moans, his sucking of my nipples and the sounds of his fingers getting wetter as he explored me. It was at this point, he said, “I am losing it, please let me fuck you”.

I felt flustered, I was hoping he could wait so that we could at least have oral sex before we get to it. He stopped what he was doing as I got off, and he looked really worried I would say no. Looking at the bulge in his pants and feeling like I was on fire inside, I said yes and enthusiastically helped him get his pants off. Without much further ado, he put on a condom and gently pushed me on the bed, lifted my legs and started to rub his cock on my vagina, the sounds it made when in contact with my juices were driving me insane, he proceeded to rub it on my vagina in an up-down motion and I was really feeling excited and tense. Then he started to push it in. I gasped as I tensed so hard that he couldn’t really get in. He continued to rub his cock on me as he kissed me and told me to relaxed. He tried to push in again and this time, I tried to not tense up.

In he went as we both moaned. He moved in and out of me gently as he inched more of himself into me. I was gripping a pillow over my head as he did this. As the discomfort of having something foreign enter me start to subside, I started to feel pulsation and rawness as he started to pick up the pace. As he went harder, faster and rougher, he pulled the pillow off my face and told me he needed to see me. I was tearing and moaning while he looked super red in the face. He started to slow down but he pumped into me harder than before and reached down to kiss me. He also brought my fingers down to my clit and told me to rub it. As he gave a few final pumps, I think he came really hard as his body shook. After thrusting into me so slowly, removing his cock out of me in a swift motion shocked my body and I think I started to cum. It was as if I could not control my body as I felt myself vibrating. He removed his very full condom and told me that he loved my tight pussy. Then started to get on top of me again and he was still semi hard. Since I was barely recovering from my intense first time, I told him I can’t do more and he told me it was ok. He proceeded to lavish my body with kisses and we slept together that night but there was no more sex. Though he did finger me and played with my breast throughout the night. He left early the next morning.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? I realised I didn’t have anything for him beyond lust and regretted that I didn’t have him go down on me while we were doing it. I do thank him for all the breast play, it was one of the most enjoyable things ever.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, To feel better about myself

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? I don’t know / I’m not sure

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? My housemates. They were not thrilled about me losing my virginity to some stranger.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

Did you get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? A little bit

Why do you regret this hookup? Feels like I threw 30 years of waiting on a stranger

What was the BEST thing about this hookup? Learning about my body and he has made me a breast play fanatic. Since that night, I have been playing with my breasts when I masturbate.

What was the WORST thing about this hookup? I wish I had someone I had a real connection with

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I surprised myself with my sexual assertiveness to tell him what I want in the moment.

All things considered, how POSITIVE was this experience? Somewhat positive

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup? We are no longer in contact. He just isn’t for me.

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? No opinion

What do you think about the Casual Sex Project? Good to have a platform to share sex positivity

You have a hookup story to share? Submit it here!